Nestled in the heart of Florida, the picturesque Lake Hollingsworth area has become an enticing haven for Chicago residents seeking refuge from the biting cold of their city's winters. This charming neighborhood, located in Lakeland, offers not only a respite from the frosty winds but also the opportunity to own homes with a pool that can be enjoyed year-round. Let's explore how the Lake Hollingsworth area has captured the hearts of Chicagoans and why it's considered a winter sanctuary.

The Allure of Lake Hollingsworth

Lake Hollingsworth is a gem among Florida's many lakes, known for its serene beauty and captivating sunsets. The neighborhood that surrounds it boasts lush greenery, elegant homes, and a welcoming community spirit that immediately draws newcomers in. But what sets it apart and makes it a winter destination for Chicagoans?

Escaping the Cold

Chicago winters are legendary for their bone-chilling temperatures and heavy snowfall. Many residents dream of escaping the frigid climate, even if only temporarily. Lake Hollingsworth's mild winters, characterized by warm temperatures and abundant sunshine, offer a stark contrast to the snow-covered streets of Chicago.

Year-Round Poolside Living

One of the neighborhood's standout features is the prevalence of homes with private pools. Chicagoans are no strangers to the joys of summer pool parties, but Lake Hollingsworth takes it a step further by allowing residents to enjoy their pools year-round. With Florida's temperate climate, a dip in the pool is a possibility even in the middle of winter.

Real Estate Opportunities

Lake Hollingsworth has seen a surge in real estate interest from Chicago buyers in recent years. The lure of owning a home in this charming neighborhood, complete with a pool and the promise of endless summer-like days, is undeniable. While many Chicagoans initially visit as snowbirds, they often find themselves enchanted enough to become full-time residents.


Lake Hollingsworth offers a strong sense of community, with friendly neighbors and an active outdoor lifestyle. The lake itself is a central hub for outdoor activities, such as jogging and cycling arounds its 2.9 mile path. The area is also home to fine dining, shopping, and cultural attractions that keep residents entertained year-round. It's location just south of Downtown Lakeland offers plenty of entertainment and dining options.

A Winter Sanctuary

For Chicago residents who've endured months of shoveling snow and bundling up in layers, Lake Hollingsworth provides a welcome escape. The chance to relax by their own pool, basking in the Florida sun while their northern counterparts endure the frost, is a dream come true.

Lake Hollingsworth's allure as a winter haven for Chicago residents seeking year-round poolside living is undeniable. Its natural beauty, mild climate, real estate opportunities, and welcoming community make it a desirable destination for those looking to escape the cold. As Chicagoans continue to discover the charms of Lake Hollingsworth, this Florida neighborhood is likely to remain a popular retreat for winters to come.

Check out all the Homes For Sale in the Lake Hollingsworth Area